Aluminum(III) Chloride → HCID 22139220, compound

HRID 1825748Notes

Reaction equation

HRID 1825748 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Cl-].[Cl-].[Al+3].[CH3:11][O:12][CH2:13][CH2:14][NH:15][C:16]([C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[CH:23][NH:24]2)=[CH:20][CH:19]=1)=O>O1CCCC1>[CH3:11][O:12][CH2:13][CH2:14][NH:15][CH2:16][C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[CH:23][NH:24]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 22139247HCID 22139247, compound

Product 1

HCID 22139220HCID 22139220, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (0.93 g, 24.5 mmol) in anhydrous tetrahydrofurane (15 ml), aluminum trichloride (3.5 g, 24.5 mmol) was added portionwise at 0° C. for 30 min and then 6-[N-(2-methoxyethyl)carbamoyl]indole (1 g, 4.5 mmol) was added portionwise at 0° C. for 1 h. After stirring overnight at room temperature, the reaction mixture was quenched with 20% NaOH while cooling in ice water. The precipitate was filtered and washed with dichloromethane and the solvent evaporated after dried over anhydrous sodium sulfate. The residue was chromatographed on silica gel (eluent, dichloromethane:methanol, 9:1) and then the product was precipitated with hexane to give 0.3 g (32%) of 6-[(2-methoxyethyl)aminomethyl]indole.

Workup

  1. additionwas added portionwise at 0° C. for 30 min
  2. customthe reaction mixture was quenched with 20% NaOH
  3. temperaturewhile cooling in ice water
  4. filtrationThe precipitate was filtered
  5. washwashed with dichloromethane
  6. customthe solvent evaporated
  7. dry with materialafter dried over anhydrous sodium sulfate
  8. customThe residue was chromatographed on silica gel (eluent, dichloromethane:methanol, 9:1)
  9. customthe product was precipitated with hexane

Sources & evidence

ORD record
ord-a29f0f635f8140a4abb43999f35e15ec
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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